


First Hand Know-How

by iceprinceloki



Series: Stress Relief [34]
Category: Supernatural
Genre: Bi-Curious Dean Winchester, Curious Sam, M/M, Teen Dean, Teen Sam, Teen Years, Unresolved Sexual Tension
Language: English
Status: Completed
Published: 2016-08-03
Updated: 2016-08-03
Packaged: 2018-07-29 04:45:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 1,097
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7670617
Author URL: https://archiveofourown.org/users/iceprinceloki/pseuds/iceprinceloki
Summary: <blockquote class="userstuff">
              <p>Sam has a mystery man-crush and questions that only Dean could have first hand know-how on.</p>
            </blockquote>





	First Hand Know-How

**Author's Note:**

> Requested by SingingWithSherlock! I hope you enjoy it! Rated E to be safe!

Sam edged into Dean’s room nervously and cleared his throat to get his brothers attention.

Dean turned to him with a surprised expression. “Hey Sammy, you’re up past curfew, what’s up?”

 

Sam took a deep breath to steady himself. “Can I talk to you about something?”

“Yea sure kiddo?” The nineteen year old leaned back against his headboard and put his walkman on the bedside table.

Sam looked around the room. They’d been in the area for four months and John had been able to afford an apartment with enough rooms for all three of them. Dean had immediately taken to the idea and spent a lot of time in his room. Sam hadn’t taken it so easy, unable to sleep without the sound of Dean’s breathing in the room.

Sam sat down at the foot of Dean’s bed and crossed his legs. “Dean have you ever wanted to do something with someone but you couldn’t because you didn’t know how or if it’d be okay?”

Dean blinked in surprise and nodded. “Yea I have Sammy, everyone gets that at some point in their lives. Why? Is there a pretty girl you can’t quite go down on?” He laughed teasingly.

Sam blushed and shook his head, mumbling an explanation under his breath.

“Sammy I don’t speak grungy teenage mumbles, you’re gonna have to switch to english if you want help.”

Sam groaned in embarrassment. “It’s not a girl.”

There was complete silence for a whole five minutes. Sam anxiously looked up to find a thoughtful look on his brothers face that didn’t belong there.

“Does dad know?”

Sam shook his head rapidly “I can barely tell you this, why would I tell dad?!”

Dean shrugged. “That’s probably a good way to keep it Sam. Dad doesn’t like that kind of stuff, if he knew we were doing it he’d flip.”

“We?” Sam perked up curiously.

Dean ducked his head. “Uh shouldn’t you be in bed?”

“You’ve done it with a boy!” Sam exclaimed excitedly. “This is great! You can tell me everything I need to know! We can share stories and tips and stuff! I don’t have to keep it a secret anymore.”

“Sam stop!” Dean shouted over the noise the younger boy was making. “We are not doing that. Dad can never know. No one can ever know okay?”

Sam looked so disappointed that Dean almost took it all back.

“Yea I had sex with a guy but it is none of your business.” Dean said seriously. “I know what it’s like not knowing anything about what you want. For that reason I will hear any questions you’ve got. It’ll just be for tonight so if you wanna ask something this is your one and only chance.”

Sam nodded quickly and thought hard for a question. “What’s it like when a guy is in you?”

Dean gave Sam a level look. “It’s hard to describe but it’s good. It’s a heavy feeling and it burns a little at first but then you start moving and it gets better. The emotions are what make it better or worse though, if you enjoy being with the guy the sex is great because he’s yours and you’re cementing that fact in his head. If you’re just hooking up it’s not as fun.”

“So you don’t feel things like girls do? I mean I heard that girls have a spot inside that feels good.”

Dean rubbed a hand over his face. “Do guys have vagina’s Sam?”

“No?”

“Then don’t compare them to girls. Guys have prostates but it’s not always nice to have that touched, it gets too much too soon.”

Sam gave Dean a curious look and opened his mouth but Dean cut him off instantly. “No I’m not sharing my personal experience.”

“What do I do if he wants me to go down and it’s too big for my mouth?” Sam covered his face as he finished his sentence.

Dean bit back a laugh with all his might and answered steadily. “Use your hands on what doesn’t fit, no one says you have to take it all. Just remember to keep your teeth covered with your lips!”

Sam blushed hotly and nodded. He took a moment to mull it all over before asking his next question. “It’s it better than with a girl?”

“That depends on you Sam. Everyone experiences sex differently and everyone you sleep with will give you a different experience. If you like it rough then guys are usually more game but there are girls who go for that too.” Dean smiled in amusement at his little brother.

“What if I like it better with guys?”

The question threw Dean off his game and he gave Sam a lost look. “What do you mean Sam?”

“Would it be bad? Pastor Jim says it’s wrong and dad doesn’t like it...” Sam fiddled with the hem of his shirt awkwardly while he spoke.

“There’s nothing wrong with liking one flavour more Sammy, it doesn’t change you as a person.” Dean said gently. “You’re an amazing kid and anyone who meets you will say that, shucking up with men won’t change anyone’s opinion about you. If it does they weren’t worth your time to begin with.”

Sam hugged his brother tightly and nuzzled against his chest. “Thanks Dean.”

“No problem kiddo, that’s what I’m here for; embarrassing talks after bedtime.”

Sam laughed and drew away regretfully.

“Can I ask one question Sam?” At Sam’s nod Dean continued. “Who is the guy you’re thinking about doing all this stuff with?”

Sam grinned shyly and shrugged. “Just a boy I used to go to school with, we were pretty close before we moved here, and I wanted to get back in touch; since we’re not together a lot anymore.”

Dean shrugged lightly and nodded his approval. “As long as he’s good people. If he hurts you tell me and I’ll set him on the straight and narrow..”

“You wouldn’t know the straight and narrow if it was under your nose!” Sam laughed. “You’d get lost looking for it and end up shucking up with him before I can!”

Dean laughed and pushed Sam to stand up. “Go to bed Bitch!”

“Jerk!” Sam threw back as he ran out of the room.

Dean sat laughing for a while after that and lay back on his bed. Sam was growing up fast and he was happy to be included in the other boy’s life, it was hard being separated most of the day so it was good to catch up and talk.

**Author's Note:**

> Accio Comments!


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